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    Amitriptyline Hydrochloride

    ACTIVE PHARMA INGREDIENTS

    DEVELOPMENTS

    INTERMEDIATES

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    2D Structure
    Also known as: 549-18-8, Amitriptyline hcl, Annoyltin, Tryptizol, Domical, Syneudon
    Molecular Formula
    C20H24ClN
    Molecular Weight
    313.9  g/mol
    InChI Key
    KFYRPLNVJVHZGT-UHFFFAOYSA-N
    FDA UNII
    26LUD4JO9K
    Tricyclic antidepressant with anticholinergic and sedative properties. It appears to prevent the re-uptake of norepinephrine and serotonin at nerve terminals, thus potentiating the action of these neurotransmitters. Amitriptyline also appears to antagonize cholinergic and alpha-1 adrenergic responses to bioactive amines.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    N,N-dimethyl-3-(2-tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,11,13-hexaenylidene)propan-1-amine;hydrochloride
    2.1.2 InChI
    InChI=1S/C20H23N.ClH/c1-21(2)15-7-12-20-18-10-5-3-8-16(18)13-14-17-9-4-6-11-19(17)20;/h3-6,8-12H,7,13-15H2,1-2H3;1H
    2.1.3 InChI Key
    KFYRPLNVJVHZGT-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CN(C)CCC=C1C2=CC=CC=C2CCC3=CC=CC=C31.Cl
    2.2 Other Identifiers
    2.2.1 UNII
    26LUD4JO9K
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Amineurin

    2. Amitrip

    3. Amitriptylin Beta

    4. Amitriptylin Desitin

    5. Amitriptylin Neuraxpharm

    6. Amitriptylin Rph

    7. Amitriptylin-neuraxpharm

    8. Amitriptyline

    9. Amitrol

    10. Anapsique

    11. Apo Amitriptyline

    12. Apo-amitriptyline

    13. Damilen

    14. Desitin, Amitriptylin

    15. Domical

    16. Elavil

    17. Endep

    18. Laroxyl

    19. Lentizol

    20. Novoprotect

    21. Rph, Amitriptylin

    22. Saroten

    23. Sarotex

    24. Syneudon

    25. Triptafen

    26. Tryptanol

    27. Tryptine

    28. Tryptizol

    2.3.2 Depositor-Supplied Synonyms

    1. 549-18-8

    2. Amitriptyline Hcl

    3. Annoyltin

    4. Tryptizol

    5. Domical

    6. Syneudon

    7. Endep

    8. Lentizol

    9. Novoprotect

    10. Etravil

    11. Saroten

    12. Elavil Hydrochloride

    13. Amineurin

    14. Amitril

    15. Amitrip

    16. Anapsique

    17. Tryptine

    18. Amavil

    19. Amitid

    20. Ami-anelun

    21. Apo-amitriptyline

    22. Daprimen

    23. Elatrolet

    24. Maxivalet

    25. Miketorin

    26. Mitaptyline

    27. Rantoron

    28. Sarotena

    29. Trepiline

    30. Triptizol

    31. Trytomer

    32. Vanatrip

    33. Yamanouchi

    34. Amilit

    35. Amiplin

    36. Amiprin

    37. Amyline

    38. Amyzol

    39. Belpax

    40. Elatrol

    41. Enafon

    42. Etrafon

    43. Kyliran

    44. Larozyl

    45. Levate

    46. Pinsanu

    47. Pinsaun

    48. Teperin

    49. Triavil

    50. Tridep

    51. Tripta

    52. Trynol

    53. Damilen Hydrochloride

    54. Amitriptyline Chloride

    55. Saroten Retard

    56. Tryptizol Retard

    57. Limbitrol Ds

    58. Tryptacap Hydrochloride

    59. Adt-zimaia

    60. Oasil-m

    61. Redomex

    62. Proheptadien Monohydrochloride

    63. Amitriptyline (hydrochloride)

    64. Sk-amitriptyline Chloride

    65. Limbitrol

    66. Sarotex

    67. Nih 10794

    68. Ccris 7092

    69. Amitryptiline Hydrochloride

    70. Nsc-104210

    71. 26lud4jo9k

    72. Annolytin

    73. Mls000028437

    74. Component Of Etrafon

    75. Component Of Triavil

    76. 5-(3-(dimethylamino)propylidene) Dibenzosuberane Hcl

    77. 3-(10,11-dihydro-5h-dibenzo[a,d][7]annulen-5-ylidene)-n,n-dimethylpropan-1-amine Hydrochloride

    78. 1-propanamine, 3-(10,11-dihydro-5h-dibenzo(a,d)cyclohepten-5-ylidene)-n,n-dimethyl-, Hydrochloride

    79. Novotriptyn

    80. Nornaln

    81. Smr000058368

    82. 549-18-8 (hcl)

    83. Amitryptyline Hydrochloride

    84. 5-(3-dimethylaminopropylidene)dibenzo(a,d)(1,4)cycloheptadiene Hydrochloride

    85. Dsstox_cid_13187

    86. Dsstox_rid_79055

    87. Dsstox_gsid_33187

    88. Amitriptyline Hydrochloride 100 Microg/ml In Acetonitrile

    89. 1-propanamine, 3-(10,11-dihydro-5h-dibenzo[a,d]cyclohepten-5-ylidene)-n,n-dimethyl-, Hydrochloride

    90. 3-(10,11-dihydro-5h-dibenzo[a,d][7]annulen-5-ylidene)-n,n-dimethyl-1-propanamine Hydrochloride

    91. 3-(10,11-dihydro-5h-dibenzo[a,d]cyclohepten-5-ylidene)-n,n-dimethyl-1-propanamine Hydrochloride

    92. Nsc169910

    93. Wln: L C676 By&t&j Bu3n1&1 &gh

    94. Amitriptyline Hydrochloride [jan]

    95. Sr-01000003046

    96. Ncgc00015095-09

    97. Cas-549-18-8

    98. Einecs 208-964-6

    99. Mfcd00012537

    100. Amitryptylline Hydrochloride

    101. Unii-26lud4jo9k

    102. Nsc 104210

    103. Amilent

    104. Sylvemid

    105. Amicen

    106. Euplit

    107. Uxen

    108. 5-(3-dimethylaminopropylidene)dibenzo[a,4]cycloheptadiene Hydrochloride

    109. 5-[3-(dimethylamino)propylidene]dibenzo[a,4]cycloheptadiene Hydrochloride

    110. 1-propanamine,11-dihydro-5h-dibenzo[a,d]cyclohepten-5-ylidene)-n,n-dimethyl-, Hydrochloride

    111. 5-(3-dimethylaminopropylidene)dibenzo[a,d][1,4]cycloheptadiene Hydrochloride

    112. 5h-dibenzo[a,.gamma.-propylamine, 10,11-dihydro-n,n-dimethyl-, Hydrochloride

    113. 5h-dibenzo[a,.gamma.-propylamine, 10,11-dihydro-n,n-dimethyl-,hydrochloride

    114. Prestwick_20

    115. 3-(5,6-dihydrodibenzo[2,1-b:1',2'-e][7]annulen-11-ylidene)-n,n-dimethylpropan-1-amine;hydrochloride

    116. Drg-0169

    117. Elavil (tn)

    118. Amitriptyline Hydrochloride [usp:jan]

    119. Cpd000058368

    120. Opera_id_618

    121. Nortriptyline Impurity F

    122. Amitriptylini Hydrochloridum

    123. C20h23n.hcl

    124. Schembl41079

    125. 10,11-dihydro-n,n-dimethyl-5h-dibenzo(a,d)cycloheptene-delta(sup 5,gamma)-propylamine Hydrochloride

    126. Mls001055393

    127. Mls001074176

    128. Mls002222152

    129. Spectrum1500117

    130. Regid_for_cid_11065

    131. Chebi:2667

    132. Chembl1200964

    133. Dtxsid9033187

    134. Hy-b0527a

    135. Amitriptyline Hydrochloride ,(s)

    136. Amitriptyline Hydrochloride, 99%

    137. Hms1568o09

    138. Hms1920c13

    139. Pharmakon1600-01500117

    140. Bcp31573

    141. Amitriptyline-[13c3] Hydrochloride

    142. Tox21_113122

    143. Tox21_201278

    144. Tox21_303612

    145. Tox21_500112

    146. Ccg-38919

    147. Nsc104210

    148. Nsc755869

    149. S3183

    150. Akos015994716

    151. Tox21_113122_1

    152. Ks-1291

    153. Lp00112

    154. Nc00497

    155. Nsc-169910

    156. Nsc-755869

    157. Amitriptyline Hydrochloride (jp17/usp)

    158. Amitriptyline Hydrochloride [mi]

    159. Ncgc00015095-15

    160. Ncgc00024433-03

    161. Ncgc00024433-05

    162. Ncgc00093609-01

    163. Ncgc00093609-02

    164. Ncgc00093609-03

    165. Ncgc00093609-04

    166. Ncgc00093609-05

    167. Ncgc00257393-01

    168. Ncgc00258830-01

    169. Ncgc00260797-01

    170. 5h-dibenzo(a,d)cycloheptene-delta(sup 5),gamma-propylamine, 10,11-dihydro-n,n-dimethyl-, Hydrochloride

    171. 5h-dibenzo(a,d)cycloheptene-delta5,gamma-propylamine, 10,11-dihydro-n,n-dimethyl-, Hydrochloride

    172. Amitriptyline Hydrochloride [hsdb]

    173. Ba164159

    174. N,n-dimethyl-3-(2-tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,11,13-hexaenylidene)propan-1-amine;hydrochloride

    175. Amitriptyline Hcl;nortriptyline Impurity F

    176. Amitriptyline Hydrochloride [mart.]

    177. Amitriptyline Hydrochloride [vandf]

    178. Amitriptyline Hydrochloride [usp-rs]

    179. Amitriptyline Hydrochloride [who-dd]

    180. Amitriptyline Hydrochloride [who-ip]

    181. A0908

    182. Eu-0100112

    183. Ft-0662108

    184. Ft-0662109

    185. Sw196337-3

    186. A 8404

    187. A16404

    188. D00809

    189. D81789

    190. Amitriptyline Hydrochloride [ep Impurity]

    191. A854879

    192. Amitriptyline Hydrochloride [ep Monograph]

    193. Amitriptyline Hydrochloride [usp Impurity]

    194. Amitriptyline Hydrochloride [usp Monograph]

    195. Amitriptylini Hydrochloridum [who-ip Latin]

    196. Amitriptyline Hydrochloride, >=98% (tlc), Powder

    197. Sr-01000003046-2

    198. Sr-01000003046-6

    199. W-105596

    200. Etrafon-a Component Amitriptyline Hydrochloride

    201. Limbitrol Component Amitriptyline Hydrochloride

    202. Q27254112

    203. Amitriptyline Hydrochloride Component Of Etrafon-a

    204. Amitriptyline Hydrochloride Component Of Limbitrol

    205. F0001-1443

    206. Limbitrol Ds Component Amitriptyline Hydrochloride

    207. Amitriptyline Hydrochloride Component Of Limbitrol Ds

    208. 5-[3-(dimethylamino)propylidene]dibenzosuberane Hydrochloride

    209. Amitriptyline Hydrochloride 1.0 Mg/ml In Methanol (as Free Base)

    210. Amitriptyline Hydrochloride, Drug Standard, 1.0 Mg/ml In Methanol

    211. Amitriptyline Hydrochloride, British Pharmacopoeia (bp) Reference Standard

    212. Amitriptyline Hydrochloride, European Pharmacopoeia (ep) Reference Standard

    213. Amitriptyline Hydrochloride, Pharmaceutical Secondary Standard; Certified Reference Material

    214. Amitriptyline Hydrochloride, United States Pharmacopeia (usp) Reference Standard

    215. 1-propanamine, 3-(10,11-dihydro-5h-dibenzo(a,d)cyclohepten-5-ylidene)-n,n-dimethyl-, Hydrochloride (1:1)

    216. 10,11-dihydro-n,n-dimethyl-5h-dibenzo[a,d]cycloheptene-delta5,gamma-propylamine Hydrochloride

    217. 3-(10,11-dihydro-5h-dibenzo[a,d]cyc Lohepten-5-ylidene)-n,n-dimethyl-1-propanamine Hydrochloride

    218. 5h-dibenzo[a,d]cycloheptene-delta(sup5),gamma-propylamine, 10,11-dihydro-n,n-dimethyl-, Hydrochloride

    219. 5h-dibenzo[a,d]cycloheptene-delta5,gamma-propylamine, 10,11-dihydro-n,n-dimethyl-, Hydrochloride (6ci,8ci)

    220. Amitriptyline Hydrochloride Solution, 1.0 Mg/ml In Methanol, Ampule Of 1 Ml, Certified Reference Material

    221. N,n-dimethyl-3-(2-tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,11,13-hexaenylidene)propan-1-amine;hydron;chloride

    2.4 Create Date
    2005-06-08
    3 Chemical and Physical Properties
    Molecular Weight 313.9 g/mol
    Molecular Formula C20H24ClN
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count1
    Rotatable Bond Count3
    Exact Mass313.1597275 g/mol
    Monoisotopic Mass313.1597275 g/mol
    Topological Polar Surface Area3.2 Ų
    Heavy Atom Count22
    Formal Charge0
    Complexity331
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NameAmitriptyline hydrochloride
    Drug LabelDESCRIPTIONAmitriptyline HCl is 3-(10,11-dihydro-5H-dibenzo [a,d] cycloheptene-5-ylidene)-N,N-dimethyl-1-propanamine hydrochloride. Its empirical formula is C20H23NHCl, and its structural formula isAmitriptyline HCl, a dibenzocycloheptadiene deriv...
    Active IngredientAmitriptyline hydrochloride
    Dosage FormTablet
    Routeoral; Oral
    Strength75mg; 100mg; 25mg; 50mg; 10mg; 150mg
    Market StatusPrescription
    CompanyVintage Pharms; Mutual Pharm; Sun Pharm Inds; Sandoz; Mylan

    2 of 2  
    Drug NameAmitriptyline hydrochloride
    Drug LabelDESCRIPTIONAmitriptyline HCl is 3-(10,11-dihydro-5H-dibenzo [a,d] cycloheptene-5-ylidene)-N,N-dimethyl-1-propanamine hydrochloride. Its empirical formula is C20H23NHCl, and its structural formula isAmitriptyline HCl, a dibenzocycloheptadiene deriv...
    Active IngredientAmitriptyline hydrochloride
    Dosage FormTablet
    Routeoral; Oral
    Strength75mg; 100mg; 25mg; 50mg; 10mg; 150mg
    Market StatusPrescription
    CompanyVintage Pharms; Mutual Pharm; Sun Pharm Inds; Sandoz; Mylan

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Analgesics, Non-Narcotic

    A subclass of analgesic agents that typically do not bind to OPIOID RECEPTORS and are not addictive. Many non-narcotic analgesics are offered as NONPRESCRIPTION DRUGS. (See all compounds classified as Analgesics, Non-Narcotic.)

    Antidepressive Agents, Tricyclic

    Substances that contain a fused three-ring moiety and are used in the treatment of depression. These drugs block the uptake of norepinephrine and serotonin into axon terminals and may block some subtypes of serotonin, adrenergic, and histamine receptors. However, the mechanism of their antidepressant effects is not clear because the therapeutic effects usually take weeks to develop and may reflect compensatory changes in the central nervous system. (See all compounds classified as Antidepressive Agents, Tricyclic.)

    Adrenergic Uptake Inhibitors

    Drugs that block the transport of adrenergic transmitters into axon terminals or into storage vesicles within terminals. The tricyclic antidepressants (ANTIDEPRESSIVE AGENTS, TRICYCLIC) and amphetamines are among the therapeutically important drugs that may act via inhibition of adrenergic transport. Many of these drugs also block transport of serotonin. (See all compounds classified as Adrenergic Uptake Inhibitors.)

    5.2 FDA Pharmacological Classification
    5.2.1 Pharmacological Classes
    Tricyclic Antidepressant [EPC]